Chelsea Handler revealed she ended her four-year relationship with ex-boyfriend Ted Harbert after having a threesome with him and a female masseuse.
During their ménage à trois, the 48-year-old comedian recalled feeling ‘very turned on by this woman’ as she detailed the experience for the first time on Wednesday’s episode of SiriusXM’s Andy Radio.
‘I ended up hooking up with her several times without the guy,’ she confessed. ‘That’s when I knew it was time to break up with the guy.’
The former late-night talk show host went on to admit that she never told Harbert, 67, that she continued having a sexual relationship with their massage therapist.
When asked if she would consider adding another lover in the bedroom with her next partner, the New Jersey native called the encounter ‘fun’ and stated she would be interested in having another.
Opening up: Chelsea Handler revealed she ended her four-year relationship with ex-boyfriend Ted Harbert after having a threesome with him and a female masseuse
The beginning of the end: During their ménage à trois, the 48-year-old comedian recalled feeling ‘very turned on by this woman’ as she detailed the experience for the first time on Wednesday’s episode of SiriusXM’s Andy Radio; seen in 2008
‘I don’t want to get double-teamed by a guy, but I would like another girl in the situation,’ she said. ‘You know? She can do all the stuff that I’m too f**king lazy to do.’
Still, Handler then expressed she would ‘question’ why a male partner would want ‘penetration’ from another man.
‘Maybe oral is less questionable. I don’t know,’ she told listeners. ‘I’ve never been up against this kind of conundrum.’
The People’s Choice Award winner, who has been romantically linked to rapper 50 Cent and Andre Balazs, clarified that has ‘slept with a woman’ but ‘hasn’t dated a woman.’
The bestselling author previously stated that her and Harbert split because they struggled to separate business and pleasure.
‘I would come home from work, and Ted would be like, ‘Do you want to watch your show?’ and I’d be like, ‘No, I just came from my show. That’s the last thing I’d want to do,” she told THR in 2012. ‘That was the reason it didn’t work out, ultimately. I think.’
Handler’s relationship with the broadcasting and television executive, who was serving as CEO of Comcast Entertainment Group, at the time, began in 2006.
That same year, her hit series, The Chelsea Handler Show, ran from 2007 to 2014 on the E! network.
‘I ended up hooking up with her several times without the guy,’ she confessed. ‘That’s when I knew it was time to break up with the guy’ (seen on January 15, 2023)
Secret: The former late-night talk show host went on to admit that she never told Harbert, 67, that she continued having a sexual relationship with their massage therapist; seen in 2007
After calling it quits in 2010, he went on to marry Lisa Medrano the following year.
Back in 2014, when asked by Barbara Walters if she would ‘consider having a relationship with a woman,’ the TV personality responded: ‘I’m not a lesbian.’
‘I wish I was [a lesbian],’ she quipped. “I would help you. I would try to make this interview even more exciting.”
She most recently dated Jo Koy for a year, before announcing they broke up in in July 2022.
Strictly sexual: The People’s Choice Award winner, who has been romantically linked to rapper 50 Cent and Andre Balazs, clarified that has ‘slept with a woman’ but ‘hasn’t dated a woman’ (seen in 2023)
While speaking about her relationship with the comedian, 52, Handler said: ‘I’ve changed so much and my love was so big that it just blew me open. And as painful as the ending of something like that is, I’m so well-versed in therapy and understanding that every door shutting is a new beginning and I do believe it.’
‘I still believe that my person is coming, whether that is Jo Koy at a certain time or if it’s not, I accept that. I love him and he’s in his own path,’ she said on the podcast, We Can Do Hard Things with Glennon Doyle.
Still, the star said it has ‘it’s been an emotional rollercoaster’ but that their relationship was just ‘not working.’
‘I’m not going to abandon myself,’ Handler added. ‘I have to choose myself.’
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